Tunable biomimetic systems based on a novel amphiphilic pyrimidinophane and a helper nonionic surfactant

• Tunable nanosystems based on a water insoluble pyrimidinic amphiphile are designed.
• Nonionic surfactant Triton-X-100 increases mixed aggregate stability.
• New candidates for nanocarriers of negatively charged biosubstrates were suggested.

Tunable nanosystems based on a novel water insoluble pyrimidinic amphiphile are designed. pH dependent aggregates composed of protonated pyrimidinophane 1 are formed at pH < 4, which undergo reversible transition to precipitate at neutral and basic conditions. The approach assuming the application of a helper nonionic surfactant Triton-X-100 (TX-100) is used in this work. Different models of a self-assembly were found depending on the molar ratio of components and solution pH. In the equimolar 1 − TX-100 solution, mixed assemblies contributed by aggregated molecules of both TX-100 and cationic form of 1 are formed in acidic conditions. Upon alkalization, deprotonated pyrimidinophane molecules shift toward the micellar core. The assemblies undergo reversible precipitation after 4–5 h, while the excess of TX-100 leads to the formation of highly stable mixed aggregates. The acidification–alkalization cycles followed by the aggregation/precipitation and the re-charging of aggregates can be multiply repeated. Surprisingly, stable mixed aggregates are also formed under the excess of pyrimidinophane in both the acidic and alkaline conditions, but at a certain component ratio. They are characterized by the highest micellization degree among all the systems studied. The low concentration threshold of these assemblies in alkali solution is probably due to their nonionic character.

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